Visiting Associate Professor of Chemistry
B.A./M.A., Boston University, 1996
Ph.D., The University of Chicago, 2002
Phone: (321) 674-7310
Office: 220 Olin Physical Sciences Building
AWARDS and HONORS
2008, Thieme Chemistry Journals Award (Germany)
2007, University of Miami Provost Award
2006, Summer Award in the Natural Sciences and Engineering, University of Miami 2006, University of Miami Provost Award
GRANTS and CONTRACTS
2012-2016, National Science Foundation, Chemical Synthesis Program
2007-2010, James and Esther King Biomedical Research Program
2007-2008, American Cancer Society IRG
The Takenaka group is interested in synthetic organic chemistry in broad terms, which range from asymmetric catalysis to synthesis of complex natural products. New methods offer new ways to assemble the complex molecular architecture and execution of resulting new synthetic strategies, in turn, lead to new insights and discoveries in method development. Methodology and synthesis are expected to complement to each other. The group’s focus is on the design and development of conceptually new catalysts for the promotion of selective chemical transformations of broad synthetic utility. Of particular interest is the development of environmentally benign, highly versatile Lewis/Brønsted acids that catalyze carbon-carbon bond formation with the highest level of selectivity and efficiency, which is of central importance in organic synthesis. The second major focus of our program is on the synthesis of structurally interesting and biologically significant natural products that not only encompass our own synthetic methods but also inspire further methodology and strategy development, including mechanistic aspects. The objectives of such endeavors are the discovery and development of new synthetic technology that provides efficient access to potential pharmaceuticals in green, non-toxic fashion, as well as better understanding of organic chemistry.
17) Narcis, M. J.; Takenaka, N. “Helical-Chiral Small Molecules in Asymmetric Catalysis” Eur. J. Org. Chem., 2014, 21-34.
16) Peng, Z.; Narcis, M. J.; Takenaka, N. “Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts” Molecules, 2013, 18, 9982-9998.
15) Peng, Z.; Takenaka, N. “Application of Helical-Chiral Pyridines as Organocatalysts in Asymmetric Synthesis” The Chemical Record, 2013, 13, 28- 42.
14) Narcis, M. J.; Sprague, D. J.; Captain, B.; Takenaka, N. “Enantio- and periselective nitroalkene Diels-Alder reaction” Org. Biomol. Chem., 2012, 10, 9134-9136.
13) Chen, J.; Captain, B.; Takenaka, N. “Helical Chiral 2,2’-Bipyridine N-Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane” Org. Lett., 2011, 13, 1654-1657.
12) Aguado, A.; Takenaka, N. “Intramolecular Nitroalkene Diels-Alder Reaction Catalyzed by Brønsted Acids” Synlett, 2011, 9, 1259-1261.
11) Takenaka, N.; Chen, J.; Captain, B.; Sarangthem, R. S.; Chandrakumar, A. “Helical Chiral 2-Aminopyridinium Ions: A New Class of Hydrogen Bond Donor Catalysts” J. Am. Chem. Soc. 2010, 132, 4536-4537. (Highlighted in Synfact 2010, 6, 712.)
10) Chen, J.; Takenaka, N. “Helical Chiral Pyridine N-Oxides: A New Family of Asymmetric Catalysts” Chem. Eur. J. 2009, 15, 7268-7276.
9) Takenaka, N.; Sarangthem, R. S.; Captain, B. “Helical-Chiral Pyridine N-Oxides, a New Family of Asymmetric Catalysts” Angew. Chem. Int. Ed. 2008, 47, 9708- 9710. (This work was among the twelve most accessed articles of the month in Angew. Chem. Int. Ed.)
8) Takenaka, N.; Sarangthem, R. S.; Seerla, S. K. “2-Aminopyridinium Ions Activate Nitroalkenes through Hydrogen Bonding” Org. Lett., 2007, 9, 2819- 2822.
Undergraduate, Graduate and Postdoctoral Publications
7) Takenaka, N.; Abel, J. P.; Yamamoto, H. “Asymmetric Conjugate Addition of Silyl Enol Ethers Catalyzed by Tethered Bis(8-Quinolinolato) Aluminum Complexes” J. Am. Chem. Soc. 2007, 129, 742-743.
6) Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. “Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels-Alder Reactions through Hydrogen Bonding” J. Am. Chem. Soc. 2005, 127, 1336-1337.
5) Takenaka, N.; Xia, G.; Yamamoto, H. “Catalytic, Highly Enantio- and Diastereoselective Pinacol Coupling Reaction with a New Tethered Bis(8- quinolinolato) Ligand” J. Am. Chem. Soc. 2004, 126, 13198-13199.
4) Takenaka, N.; Huang, Y.; Rawal, V. H. “The First Catalytic Enantioselective Diels-Alder Reactions of 1,2-Dihydropyridine: Efficient Syntheses of Optically Active 2-Azabicyclo-[2.2.2]octanes with Chiral BINAM Derived Cr (III) Salen Complexes” Tetrahedron, 2002, 58, 8299-8305.
3) Hu, T.; Takenaka, N.; Panek, J. S. “Asymmetric Crotylation Reactions in the Synthesis of Polypropionate Derived Macrolide: Application to the Total Synthesis of Oleandolide” J. Am. Chem. Soc. 2002, 124, 12806-12815.
2) Hu, T.; Takenaka, N.; Panek, J. S. “Total Synthesis of Oleandolide” J. Am. Chem. Soc. 1999, 121, 9229-9230.
1) Jain, N. F.; Takenaka, N.; Panek, J. S. “Double-Stereodifferentiating Crotylation Reactions with Chiral (E)-Crotylsilanes. Evaluation of a New Approach for the Synthesis of Polypropionate-Derived Natural Products” J. Am. Chem. Soc. 1996, 118, 12475-12476.